Product Name

  • Name

    3-(2-Methylaminoethyl)indole

  • EINECS 200-507-9
  • CAS No. 61-49-4
  • Article Data42
  • CAS DataBase
  • Density 1.088 g/cm3
  • Solubility
  • Melting Point 87-89 °C(lit.)
  • Formula C11H14N2
  • Boiling Point 336.2 °C at 760 mmHg
  • Molecular Weight 174.246
  • Flash Point 157.1 °C
  • Transport Information
  • Appearance white to off-white shiny cryst. powder or flakes
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 61-49-4 (3-(2-Methylaminoethyl)indole)
  • Hazard Symbols
  • Synonyms Indole,3-[2-(methylamino)ethyl]- (6CI,7CI,8CI);3-(2-Methylaminoethyl)indole;3-[2-(Methylamino)ethyl]-1H-indole;Dipterine;Methyltryptamine;Monomethyltryptamine;N-Methyl-1H-indole-3-ethanamine;N-Methyltryptamine;N-Monomethyltryptamine;N10-Methyltryptamine;Nb-Methyltryptamine;Nw-Methyltryptamine;[2-(1H-Indol-3-yl)ethyl]methylamine;
  • PSA 27.82000
  • LogP 2.32070

Synthetic route

methyl 2-(1-H-indol-3-yl)ethylcarbamate
58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃;95%
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;94%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 3h; Inert atmosphere; Reflux;84%
Nb-formyltryptamine
6502-82-5

Nb-formyltryptamine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 3.25h; Heating;90%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating; Yield given;
ethyl 2-(1H-indole-3-yl)ethylcarbamate
67909-99-3

ethyl 2-(1H-indole-3-yl)ethylcarbamate

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;89%
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;86%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Reflux;85%
tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
103549-24-2

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 24h;52%
indole
120-72-9

indole

oxalyl dichloride
79-37-8

oxalyl dichloride

methylamine
74-89-5

methylamine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Stage #1: indole; oxalyl dichloride In tetrahydrofuran at 0 - 20℃;
Stage #2: methylamine In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux;
50%
2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide
2054-72-0

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Inert atmosphere; Reflux;42%
2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide
2054-72-0

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide

A

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

B

2,3-dihydro-N-methyltryptamine

2,3-dihydro-N-methyltryptamine

C

3-(2-Methylamino-ethyl)-2,3-dihydro-1H-indol-3-ol

3-(2-Methylamino-ethyl)-2,3-dihydro-1H-indol-3-ol

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Heating;A 29%
B 24%
C 36%
methyl 2-(1-H-indol-3-yl)ethylcarbamate
58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

A

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

(±)-1,1'-dimethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole
4147-36-8, 4147-37-9, 5545-89-1, 23102-84-3, 85610-66-8

(±)-1,1'-dimethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole

C

meso-Chimonanthine
4147-37-9

meso-Chimonanthine

N-methyl-2-(6-(1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-yl)-1H-indol-3-yl)ethanamine

N-methyl-2-(6-(1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-yl)-1H-indol-3-yl)ethanamine

Conditions
ConditionsYield
Stage #1: methyl 2-(1-H-indol-3-yl)ethylcarbamate With 2,2,2-trifluoroethanol; bis-[(trifluoroacetoxy)iodo]benzene at -30℃;
Stage #2: With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene Heating;
A 9%
B 13%
C 30%
D 23%
tryptamine
61-54-1

tryptamine

methyl iodide
74-88-4

methyl iodide

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

3-(2-bromoethyl)-1H-indole
3389-21-7

3-(2-bromoethyl)-1H-indole

methylamine
74-89-5

methylamine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide
442531-80-8

N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide

aniline hydrochloride
142-04-1

aniline hydrochloride

aniline
62-53-3

aniline

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With ethanol
L-abrine
526-31-8

L-abrine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
at 320℃; under 12 Torr;
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
38750-13-9

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating;
(+-)-hydroxy-indol-3-yl-acetic acid methylamide

(+-)-hydroxy-indol-3-yl-acetic acid methylamide

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride
tryptamine
61-54-1

tryptamine

phenyl halide

phenyl halide

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / aq. NaOH / CHCl3 / 3 h / 20 °C
2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / DIEA / tetrahydrofuran
2: 79 percent / lithium aluminum hydride / tetrahydrofuran / Heating
View Scheme
tryptamine
61-54-1

tryptamine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / aq. NaOH / CHCl3 / 3 h
2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: 100 percent / NaOH / H2O; CH2Cl2 / 0 °C
2.1: phenyliodine(III)bis(trifluoroacetate); CF3CH2OH / -30 °C
2.2: 9 percent / Red-Al / toluene / Heating
View Scheme
Multi-step reaction with 2 steps
1: Et3N
2: LiAlH4
View Scheme
tryptamine
61-54-1

tryptamine

N-methyl-isatoic acid-anhydride

N-methyl-isatoic acid-anhydride

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / Et3N / CH2Cl2 / 0 - 20 °C
2: 50 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
View Scheme
tryptamine hydochloride
343-94-2

tryptamine hydochloride

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH; H2O / CHCl3 / 1 h
2: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme
indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4; diethyl ether
2: 130 °C
3: LiAlH4
View Scheme
2-(3-indole)-ethanol
526-55-6

2-(3-indole)-ethanol

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; phosphorus (III)-bromide
View Scheme
phenylhydrazine
100-63-0

phenylhydrazine

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc chloride
View Scheme
tryptamine
61-54-1

tryptamine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Stage #1: tryptamine; chloroformic acid ethyl ester With sodium hydroxide In water at 20℃; for 3h;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Heating / reflux;
indole
120-72-9

indole

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 0 °C
2: water / 2 h / Cooling with ice
3: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux
View Scheme
indolyl-3-glyoxylyl chloride
22980-09-2

indolyl-3-glyoxylyl chloride

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water / 2 h / Cooling with ice
2: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux
View Scheme
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl N-methyl-N-2-[(1H-indol-3-yl)-ethyl]carbamate
264619-90-1

tert-butyl N-methyl-N-2-[(1H-indol-3-yl)-ethyl]carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;99%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2-fluoro-N-(2-methoxyethyl)-9H-purin-6-amine

2-fluoro-N-(2-methoxyethyl)-9H-purin-6-amine

N2-[2-(1H-indol-3-yl)ethyl]-N6-(2-methoxyethyl)-N2-methyl-9H-purine-2,6-diamine

N2-[2-(1H-indol-3-yl)ethyl]-N6-(2-methoxyethyl)-N2-methyl-9H-purine-2,6-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 110℃;100%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

methyl chloroformate
79-22-1

methyl chloroformate

methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate
63637-70-7

methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 23h;99%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;68%
With triethylamine Yield given;
2-bromo-thiazole-5-carboxylic acid
54045-76-0

2-bromo-thiazole-5-carboxylic acid

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

N-(2-(1H-indol-3-yl)ethyl)-2-bromo-N-methylthiazole-5-carboxamide

N-(2-(1H-indol-3-yl)ethyl)-2-bromo-N-methylthiazole-5-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;98%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide
1280171-15-4

N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;97.5%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

5,5-diethoxypentanal
79893-96-2

5,5-diethoxypentanal

1-(4,4-Diethoxy-butyl)-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline
209168-95-6

1-(4,4-Diethoxy-butyl)-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline

Conditions
ConditionsYield
In toluene for 2h; Heating;97%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Dimethyl 3-(methylthio)-1,2,4-triazine-5,6-dicarboxylate
108005-26-1

Dimethyl 3-(methylthio)-1,2,4-triazine-5,6-dicarboxylate

3-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,2,4]triazine-5,6-dicarboxylic acid dimethyl ester

3-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,2,4]triazine-5,6-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In methanol Heating;95%
carbonic acid (E)-4-bromobut-2-en-1-yl methyl ester

carbonic acid (E)-4-bromobut-2-en-1-yl methyl ester

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

C17H22N2O3
1241667-72-0

C17H22N2O3

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;95%
5-phenylfuran-2-carbaldehyde
13803-39-9

5-phenylfuran-2-carbaldehyde

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

[2-(1H-indol-3-yl)ethyl](methyl)[(5-phenylfuran-2-yl)methyl]amine

[2-(1H-indol-3-yl)ethyl](methyl)[(5-phenylfuran-2-yl)methyl]amine

Conditions
ConditionsYield
Stage #1: 5-phenylfuran-2-carbaldehyde; [2-(1H-indol-3-yl)-ethyl]-methylamine In methanol at 20℃; Molecular sieve;
Stage #2: With sodium tetrahydroborate In methanol for 1h; Molecular sieve;
95%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2-(4-(benzyloxy)phenyl)acetyl chloride
39188-62-0

2-(4-(benzyloxy)phenyl)acetyl chloride

2-(4-Benzyloxy-phenyl)-N-[2-(1H-indol-3-yl)-ethyl]-N-methyl-acetamide

2-(4-Benzyloxy-phenyl)-N-[2-(1H-indol-3-yl)-ethyl]-N-methyl-acetamide

Conditions
ConditionsYield
In dichloromethane for 1h;94.3%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

tris(3-methylbut-2-enyl)borane
36934-25-5

tris(3-methylbut-2-enyl)borane

trans-2-(1,1-dimethylallyl)-3-(2-methylaminoethyl)indoline

trans-2-(1,1-dimethylallyl)-3-(2-methylaminoethyl)indoline

Conditions
ConditionsYield
Stage #1: [2-(1H-indol-3-yl)-ethyl]-methylamine; tris(3-methylbut-2-enyl)borane at 120 - 130℃; for 4.5h;
Stage #2: With sodium hydroxide In water
94%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

C26H24N2O2
1227608-19-6

C26H24N2O2

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water at 20℃; for 0.25h; Inert atmosphere;92%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2-methoxy-1,4-naphthoquinone
2348-82-5

2-methoxy-1,4-naphthoquinone

2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,4]naphthoquinone

2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,4]naphthoquinone

Conditions
ConditionsYield
In ethanol Heating;91%
formic acid
64-18-6

formic acid

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Nb-formyl-Nb-methyltryptamine
54268-27-8

Nb-formyl-Nb-methyltryptamine

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride at 60℃; for 1h;
Stage #2: [2-(1H-indol-3-yl)-ethyl]-methylamine In dichloromethane at 20℃; for 1.5h;
90%
With acetic anhydride In diethyl ether
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

N-methyl-N-(4-carboxybutyryl)-tryptamine
75622-16-1

N-methyl-N-(4-carboxybutyryl)-tryptamine

Conditions
ConditionsYield
In benzene90%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

S-(3-phenylpropyl) 4-iodobenzenecarbothioate
1178916-17-0

S-(3-phenylpropyl) 4-iodobenzenecarbothioate

C18H17IN2O
1178916-52-3

C18H17IN2O

Conditions
ConditionsYield
With potassium phosphate; silver trifluoromethanesulfonate In acetonitrile at 70℃; for 16h;90%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide
442531-80-8

N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;90%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;71%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

methyl ethynyl ketone
1423-60-5

methyl ethynyl ketone

(E)-4-[(2-(1H-indol-3-yl)ethyl)(methyl)amino]-but-3-en-2-one

(E)-4-[(2-(1H-indol-3-yl)ethyl)(methyl)amino]-but-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 5h;90%
phthalic anhydride
85-44-9

phthalic anhydride

[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

N,N'-bis[2-(1H-indol-3-yl)-ethyl]-N,N'-dimethyl-phthalamide
521949-80-4

N,N'-bis[2-(1H-indol-3-yl)-ethyl]-N,N'-dimethyl-phthalamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide89%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride
219963-60-7

4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride

N-(2-(1H-indol-3-yl)ethyl)-4-methoxy-N-methyl-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)benzenesulfonamide

N-(2-(1H-indol-3-yl)ethyl)-4-methoxy-N-methyl-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃;88.5%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate
99528-65-1

(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate

C19H18N2O2

C19H18N2O2

Conditions
ConditionsYield
With potassium tert-butylate In methanol at 5℃; for 3h; Temperature; Reagent/catalyst;88%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

carbon monoxide
201230-82-2

carbon monoxide

2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one
67115-07-5

2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; under 760.051 Torr; for 24h; Schlenk technique;88%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

N,N-dimethyl-2-(3-cyano-pyridin-4-yl)etheneamine
67988-51-6

N,N-dimethyl-2-(3-cyano-pyridin-4-yl)etheneamine

4-((E)-2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-vinyl)-nicotinonitrile
87489-66-5

4-((E)-2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-vinyl)-nicotinonitrile

Conditions
ConditionsYield
With o-toluenesulfonic acid In toluene for 72h; Heating;87%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2-iodo-N-methyltryptamine

2-iodo-N-methyltryptamine

Conditions
ConditionsYield
With chloroamine-T; potassium iodide In chloroform for 0.0833333h;87%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2,3-dihydro-N-methyltryptamine

2,3-dihydro-N-methyltryptamine

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid at 60℃; for 4h;87%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

carbon monoxide
201230-82-2

carbon monoxide

Strychnocarpine
59156-98-8

Strychnocarpine

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; for 6h;86%
With oxygen; copper diacetate; palladium diacetate In toluene at 80℃; under 760.051 Torr; for 6h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;86%
[2-(1H-indol-3-yl)-ethyl]-methylamine
61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

2-[131I]-iodo-N-methyltryptamine

2-[131I]-iodo-N-methyltryptamine

Conditions
ConditionsYield
With sodium hydroxide; [131I]-sodium iodide; chloroamine-T In chloroform for 0.05h;85.6%

3-(2-Methylaminoethyl)indole Specification

The CAS register number of 3-(2-Methylaminoethyl)indole is 61-49-4. It also can be called as N(omega)-Methyltryptamine and the IUPAC name about this chemical is 2-(1H-indol-3-yl)-N-methylethanamine. The molecular formula about this chemical is C11H14N2 and the molecular weight is 174.24. It belongs to the following product categories, such as Tryptamines; Heterocyclic Compounds and so on. When you are using it, please avoid contact with skin and eyes.

Physical properties about 3-(2-Methylaminoethyl)indole are: (1)ACD/LogP: 1.52; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -1.42; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 8.17Å2; (12)Index of Refraction: 1.621; (13)Molar Refractivity: 56.3 cm3; (14)Molar Volume: 160 cm3; (15)Polarizability: 22.32x10-24cm3; (16)Surface Tension: 45.2 dyne/cm; (17)Enthalpy of Vaporization: 57.93 kJ/mol; (18)Boiling Point: 336.2 °C at 760 mmHg; (19)Vapour Pressure: 0.000114 mmHg at 25°C.

Preparation: this chemical can be prepared by N-(2-indol-3-yl-ethyl)-formamide. This reaction will need reagent LiAlH4.

Uses of 3-(2-Methylaminoethyl)indole: it can be used to produce 2-iodo-N-methyltryptamine. This reaction will need reagent aq. chloramine-T, KI and solvent CHCl3 with reaction time of 5 min. The yield is about 87%.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc2c1c(cn2)CCNC
(2)InChI: InChI=1/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
(3)InChIKey: NCIKQJBVUNUXLW-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
(5)Std. InChIKey: NCIKQJBVUNUXLW-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 158mg/kg (158mg/kg) BEHAVIORAL: EXCITEMENT Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976.
 

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